ChemSpider 2D Image | (+)-Aureothin | C22H23NO6

(+)-Aureothin

  • Molecular FormulaC22H23NO6
  • Average mass397.421 Da
  • Monoisotopic mass397.152527 Da
  • ChemSpider ID5029106

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 1 of 1 defined stereocentres

More details:

Featured data source
The Merck Index Online

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(+)-Aureothin
2-Methoxy-3,5-dimethyl-6-{(2R,4Z)-4-[(2E)-2-methyl-3-(4-nitrophenyl)-2-propen-1-yliden]tetrahydro-2-furanyl}-4H-pyran-4-on [German] [ACD/IUPAC Name]
2-Methoxy-3,5-dimethyl-6-{(2R,4Z)-4-[(2E)-2-methyl-3-(4-nitrophenyl)-2-propen-1-ylidene]tetrahydro-2-furanyl}-4H-pyran-4-one [ACD/IUPAC Name]
2-Méthoxy-3,5-diméthyl-6-{(2R,4Z)-4-[(2E)-2-méthyl-3-(4-nitrophényl)-2-propén-1-ylidène]tétrahydro-2-furanyl}-4H-pyran-4-one [French] [ACD/IUPAC Name]
2-Methoxy-3,5-dimethyl-6-{(2R,4Z)-4-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]tetrahydrofuran-2-yl}-4H-pyran-4-one
4H-Pyran-4-one, 2-methoxy-3,5-dimethyl-6-[(2R,4Z)-tetrahydro-4-[(2E)-2-methyl-3-(4-nitrophenyl)-2-propen-1-ylidene]-2-furanyl]- [ACD/Index Name]
Aureothin
2-methoxy-3,5-dimethyl-6-((R,Z)-4-((E)-2-methyl-3-(4-nitrophenyl)allylidene)tetrahydrofuran-2-yl)-4H-pyran-4-one
2-methoxy-3,5-dimethyl-6-[(2R,4Z)-tetrahydro-4-[(2E)-2-methyl-3-(4-nitrophenyl)-2-propen-1-ylidene]-2-furanyl]-4H-pyran-4-one
2-methoxy-3,5-dimethyl-6-[(2R,5Z)-5-[(E)-2-methyl-3-(4-nitrophenyl)prop-2-enylidene]oxolan-2-yl]pyran-4-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

ZINC04025640 [DBID]
  • Miscellaneous

    • Chemical Class:

      A C-nitro compound that is (3Z)-3-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]tetrahydrofuran which is substituted by a 6-methoxy-3,5-dimet; hyl-4-oxo-4H-pyran-2-yl group at position 5. It is isolated from the soil bacterium, Streptomyces thioluteus and exhibits antitumor, antifungal, and insecticidal activi; ties. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:80024
      A C-nitro compound that is (3Z)-3-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]tetrahydrofuran which is substituted by a 6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl group at position 5. It is is olated from the soil bacterium, Streptomyces thioluteus and exhibits antitumor, antifungal, and insecticidal activities. ChEBI CHEBI:80024

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point: 591.4±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 88.2±3.0 kJ/mol
Flash Point: 235.0±32.1 °C
Index of Refraction: 1.594
Molar Refractivity: 106.4±0.4 cm3
#H bond acceptors: 7
#H bond donors: 0
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 4.32
ACD/LogD (pH 5.5): 4.06
ACD/BCF (pH 5.5): 721.15
ACD/KOC (pH 5.5): 3867.01
ACD/LogD (pH 7.4): 4.06
ACD/BCF (pH 7.4): 721.15
ACD/KOC (pH 7.4): 3867.01
Polar Surface Area: 91 Å2
Polarizability: 42.2±0.5 10-24cm3
Surface Tension: 50.3±5.0 dyne/cm
Molar Volume: 313.5±5.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™ 

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  4.78

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  515.75  (Adapted Stein & Brown method)
    Melting Pt (deg C):  219.95  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.05E-011  (Modified Grain method)
    Subcooled liquid VP: 1.09E-008 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  0.1065
       log Kow used: 4.78 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  10.717 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Ketones
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.24E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.444E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.78  (KowWin est)
  Log Kaw used:  -9.038  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.818
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.7820
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1028  (months      )
   Biowin4 (Primary Survey Model) :   3.1145  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.4369
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.5893
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  1.45E-006 Pa (1.09E-008 mm Hg)
  Log Koa (Koawin est  ): 13.818
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.06 
       Octanol/air (Koa) model:  16.1 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.987 
       Mackay model           :  0.994 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 363.7140 E-12 cm3/molecule-sec
      Half-Life =     0.029 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    21.174 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =  2688.692383 E-17 cm3/molecule-sec
      Half-Life =     0.000 Days (at 7E11 mol/cm3)
      Half-Life =      0.614 Min
   Fraction sorbed to airborne particulates (phi): 0.99 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  95.3
      Log Koc:  1.979 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.983 (BCF = 960.9)
       log Kow used: 4.78 (estimated)

 Volatilization from Water:
    Henry LC:  2.24E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.211E+007  hours   (2.171E+006 days)
    Half-Life from Model Lake : 5.684E+008  hours   (2.369E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              69.53  percent
    Total biodegradation:        0.62  percent
    Total sludge adsorption:    68.91  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.00024         0.0101       1000       
   Water     10.4            1.44e+003    1000       
   Soil      70.2            2.88e+003    1000       
   Sediment  19.4            1.3e+004     0          
     Persistence Time: 1.99e+003 hr

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